Speaker 1: What do you do in life doesn't go according to
Speaker 1: plan that moment you lose a job, or a loved one,
Speaker 1: or even a piece of yourself. I'm Brookshields and this
Speaker 1: is now What, a podcast about pivotal moments as told
Speaker 1: by people who lived them. Each week, I sit down
Speaker 1: with a guest to talk about the times they were
Speaker 1: knocked off course and what they did to move forward.
Speaker 1: Some stories are funny, others are gut wrenching, but all
Speaker 1: are unapologetically human and remind us that every success and
Speaker 1: every setback is accompanied by a choice, and that choice
Speaker 1: answers one question. Now, what at this point you had?
Speaker 1: You wanted to go to Yale? Right? I wanted to
Speaker 1: go to Yale. I did not get into Yale, and
Speaker 1: did not get into Yale. I get rejected from Yale,
Speaker 1: which I had applied to earlier. I had all my
Speaker 1: emotional egs in that basket. I went upstairs when I
Speaker 1: got the rejection letter. It was still an analog letter
Speaker 1: in those days, obviously, and I got the little envelope.
Speaker 1: I went upstairs to the bathroom and I shaved my
Speaker 1: head with scissors and a razor. If that doesn't tell
Speaker 1: you that I was an insanely over dramatic child who
Speaker 1: really just needed to be an actor and not go
Speaker 1: to Yale. Like that just tells you it's good you
Speaker 1: didn't get into Yale. You're you're way too emotionally unstable
Speaker 1: as a seventeen year old. You just need to be
Speaker 1: an actor. That voice you just heard is none other
Speaker 1: than cal Penn. You might know him as one of
Speaker 1: the world's most famous donors and one of two stars
Speaker 1: of the Harold and Kumar franchise. But did you know
Speaker 1: he also worked in the White House. That's right, cal
Speaker 1: Penn is the king of pivots. He's done a dizzying
Speaker 1: amount of work in the industry. How Sunnyside designated Survivor,
Speaker 1: and he also worked for former President Obama. We sat
Speaker 1: down to talk about his new book, You Can't Be
Speaker 1: Serious and his incredible journey. Thank you so much for
Speaker 1: doing this. Thank you. I'm very excited. I'm so excited
Speaker 1: to get a chance to talk to you. Um where
Speaker 1: are you? Where are you right now? I'm in New York,
Speaker 1: So I'm I'm a New Yorker. Oh all right. I
Speaker 1: was born in Jersey. I was I grew up mostly
Speaker 1: in Wayne and in a town called Freehold, which is
Speaker 1: where Bruce Springsteen is from. We went to my rival
Speaker 1: high school, I know, I know. So those are those
Speaker 1: are big claims to fame for where I grew up.
Speaker 1: And so you where high school? Did you go to
Speaker 1: Freehold Township High School? Freehold High School? Cause I went
Speaker 1: to I went to high school in Englewood, New Jersey. Um,
Speaker 1: but I commuted from the city to Englewood, which wasn't
Speaker 1: done in the eighties. It was the reverse commute. But
Speaker 1: it was crazy. It was like the one kid from
Speaker 1: from New York the city. Yeah, what was your childhood
Speaker 1: like in New Jersey? Like, it's so funny. I've I've
Speaker 1: thought about that a lot because it's the opener to
Speaker 1: this book that I wrote. And so the first draft
Speaker 1: that I turned in, I thought, and the way that
Speaker 1: I had pitched the book to my editor was, look,
Speaker 1: it's gonna be funny, Like these are stories that I've
Speaker 1: told very close friends after like beer number five, you know,
Speaker 1: and so it's just they're just gonna organically be fun charming, funny.
Speaker 1: I turned in the first draft and she goes, hey, um,
Speaker 1: this is super dark. What a dark series of chapters?
Speaker 1: And the reason being. And I know you'll appreciate this
Speaker 1: as a fellow artist. Is I feel like a lot
Speaker 1: of times, when we write things, you remember things like, Okay,
Speaker 1: what was a difficult time in childhood like? Or what
Speaker 1: was it like getting bullied in middle school? Which, by
Speaker 1: the way, when I was in middle school was not
Speaker 1: called getting bullied, it was just called eighth grade. So
Speaker 1: in writing that, I didn't realize that I was reverting
Speaker 1: back to whatever those emotions were. So the first draft
Speaker 1: of those chapters oddly read as more painful than they
Speaker 1: are because when I tell those stories verbally, they have
Speaker 1: a lot of humor, and there's a lot of obviously
Speaker 1: perspective of being a forty something year old who can
Speaker 1: look back at childhood with a lot of good humor.
Speaker 1: Well that's interesting because one of the things that struck
Speaker 1: me the most is your positivity through all of it,
Speaker 1: you know, and that there's this real joy in just
Speaker 1: everything and really understanding it. I can understand how it
Speaker 1: seems like these are rough stories because you're talking about
Speaker 1: stories of being bullied eighth grade. There is something in that,
Speaker 1: But to find humor through all of it is a
Speaker 1: through line. And yet I tell my kids stories like,
Speaker 1: you know, I walked into my dorm in college and
Speaker 1: my roommates had taken my Brook doll, because you know,
Speaker 1: I had a doll after me in the eighties, as
Speaker 1: one does, and it was hanging by a little news
Speaker 1: and it's like, it sounds horrible and it was funny.
Speaker 1: But when I tell my daughters things like this, they
Speaker 1: get so upset and they get so so so sad.
Speaker 1: But I learned from a very very early age the
Speaker 1: p our hum For me, that was how I survived.
Speaker 1: When did you realize you were funny? The eighth grade
Speaker 1: and sort of by force, I was the tin man
Speaker 1: and our school's production of the Whiz Uh. And you know,
Speaker 1: at the time, if you were in the school play,
Speaker 1: or if you were a soccer player, you stayed after
Speaker 1: school for your either soccer practice or rehearsal. So that
Speaker 1: late bus that took all the kids home was where
Speaker 1: all the tormenting would happen. Right, the soccer players were cool,
Speaker 1: we were not. But the tormenting, like it was things
Speaker 1: that by today's standard, thankfully, there's a way that we
Speaker 1: recognized them. Right, We were getting beat up on those busses,
Speaker 1: We were getting spit on we were getting, you know,
Speaker 1: it was just things that that we're not just the
Speaker 1: jokey thing that you can say, Oh, how silly. That
Speaker 1: was what middle school was. They were. They were certainly
Speaker 1: painful at the time. So the school play was about
Speaker 1: to go up, and you know, it was like three
Speaker 1: nights in the evening for the parents to come watch,
Speaker 1: and our drama teacher says, hey, great news, everybody. We're
Speaker 1: going to do three scenes from the play in front
Speaker 1: of the whole school during a special assembly in the afternoon.
Speaker 1: And we were all like, absolutely not, no, no way,
Speaker 1: that's that's like, this is gonna be horrible, Like we
Speaker 1: already get beat up on the bus ride home. Absolutely not.
Speaker 1: They don't need to see me in silver makeup being
Speaker 1: the tin Man, you know. And the director was like,
Speaker 1: then this play is not going up at all if
Speaker 1: you don't have the guts to do this, and so
Speaker 1: we were forced to do it. The students all come
Speaker 1: into the auditorium, they're already yelling things to make fun
Speaker 1: of us, like we can hear them from backstage, and
Speaker 1: I go out for my third scene. It was the
Speaker 1: scene when the tin Man gets his heart from the
Speaker 1: whizz or the Wizard of Us and I'm supposed to
Speaker 1: take that hard around my neck and go to the
Speaker 1: center of the stage. And the line was all you
Speaker 1: find ladies out there, watch out. And I was dreading
Speaker 1: saying this because I knew for nerdy, fourteen year old
Speaker 1: me that was just gonna be endless torment. People are
Speaker 1: just gonna repeat that line. So you've heard this phrase
Speaker 1: actors being in the zone, right. This was the first
Speaker 1: time that I remember being in the zone I apparently,
Speaker 1: and there's a video evidence of this. I had the
Speaker 1: heart around my neck. I, instead of staying in the
Speaker 1: some of the stage, walked to the very edge of
Speaker 1: the stage and in the cockiest bravado that I could muster,
Speaker 1: I looked at the audience and I said, all you
Speaker 1: find ladies out there, and then I did this massive
Speaker 1: pelvic thrust and I said watch out, and the crowd
Speaker 1: went wild. Everyone started laughing. Ladies, the girls started screaming.
Speaker 1: Everyone was on their feet applauding. It was a standing ovation.
Speaker 1: And on the bus ride on the way home, all
Speaker 1: the soccer players started applauding, and I thought they were kidding,
Speaker 1: and they said, dude, that was so funny. We had
Speaker 1: no idea that that's the kind of thing you guys
Speaker 1: were working on, and it totally just broke down this wall. Now, look,
Speaker 1: aside from the problematic nature of like why was the
Speaker 1: onus on me to not be bullied? It was well,
Speaker 1: but but you take the situation and instead of shrinking
Speaker 1: from it, you go deeper into it. For sure, reverse
Speaker 1: the narrative so that you're in control of this that
Speaker 1: you asian. So that was that sort of divine intervention
Speaker 1: of the zone totally. Did your parents come and see
Speaker 1: the performance? Yea. So they came and saw it, and
Speaker 1: I think they thought it was good. They thought it
Speaker 1: was it was fun. And did you do the hip threat? Did?
Speaker 1: I thought? I thought I was going to get in
Speaker 1: trouble when we got off stage at the assembly, and
Speaker 1: the director instead was like, that was amazing to do
Speaker 1: that again, like okay, cool, great? Uh and in hairness
Speaker 1: like that. That's why I love comedy, right, It can
Speaker 1: bring people together in a world, especially now, a world
Speaker 1: that's so polarizing, and so I still love that. And
Speaker 1: my parents didn't necessarily understand that that was a love
Speaker 1: that went beyond just a hobby, and I get it.
Speaker 1: I mean, for context, you know, their immigrants. They moved
Speaker 1: to the States in the in the early seventies, and
Speaker 1: my dad is an engineer and that was what allowed
Speaker 1: him to come to America. The fourteen year old me,
Speaker 1: of course, didn't care about any of that. I was like, okay,
Speaker 1: I don't care why you don't think the arts are
Speaker 1: a viable career. All I know is I'm this fourteen
Speaker 1: year old who was born and raised in New Jersey
Speaker 1: and I want to be an actor. So there's definitely
Speaker 1: some tension growing up there. Did you resent that at
Speaker 1: all or did you feel it or did they try
Speaker 1: to stop you in writing this book? I called my
Speaker 1: parents so many times because I wanted to talk to
Speaker 1: them about how much of what I felt was accurate.
Speaker 1: And I said, Hey, on a scale one to tend,
Speaker 1: how embarrassed were you of me when all your friends
Speaker 1: would come over for a family gathering and all the
Speaker 1: other kids would say they wanted to go to med
Speaker 1: school and people asked me, and I would say, I
Speaker 1: want to go to film school or I want to
Speaker 1: be an actor. How embarrassed on a scale one to tend?
Speaker 1: And my parents got really quiet, and they said, I
Speaker 1: don't know why you think we were embarrassed. How did
Speaker 1: you get that into your head? We were never embarrassed.
Speaker 1: We were scared because we just didn't think that somebody
Speaker 1: from our community could have a career in the arts,
Speaker 1: nor did we know that that was a viable career
Speaker 1: because we didn't have that background. I thought that was
Speaker 1: so interesting being an actor. In becoming an actor is
Speaker 1: fraught in the in the best best of all times,
Speaker 1: and whenever I hear somebody is in it, I I
Speaker 1: sort of say, oh, dear God, I'm so sorry, I'm
Speaker 1: so sorry. But you had the extra layer of of
Speaker 1: like racism in that. Can you talk a little bit
Speaker 1: about your early experience with that? That was the one
Speaker 1: piece that I hadn't necessarily anticipated. So my acting teacher
Speaker 1: had always said, you know, here are the odds. Whenever
Speaker 1: any of you start pursuing a career, you know, casting
Speaker 1: directors and producers will always only allow you to audition
Speaker 1: for things that they think you're physically right for. That's
Speaker 1: just the reality of when you start your career. It
Speaker 1: doesn't go away, by the way exactly ever, unfortunately right,
Speaker 1: And so the way that it was explained to us
Speaker 1: was like, look, and this turned out to be true. Obviously,
Speaker 1: you know, you you walk in to an audition, they're
Speaker 1: going to tell you no because you're too tall, you're
Speaker 1: too short, you're too fat, you're too skinny, all of
Speaker 1: those things, and you're just gonna have to deal with that.
Speaker 1: You can't let that get to you. What I wasn't
Speaker 1: really prepared for is that, especially in those days, and
Speaker 1: thankfully the industry has changed a lot in beautiful ways,
Speaker 1: but if you were an ethnic performer, you didn't have
Speaker 1: the luxury of being too tall, too short, too fat,
Speaker 1: too skinny, because they usually would just say, yeah, we
Speaker 1: don't want somebody who's brown. And that was super shocking
Speaker 1: to me because some of the shows that I loved
Speaker 1: that I grew up watching were like Seinfeld and Friends
Speaker 1: and shows that took place in New York City, and
Speaker 1: I didn't recognize at the time, I had no performers
Speaker 1: of color on the show, not because we didn't exist,
Speaker 1: but because the folks making those shows wanted to exclude
Speaker 1: those communities. And it was a different time. You know,
Speaker 1: I'm so glad that that doesn't exist now, not just
Speaker 1: for the sake of like people like us being able
Speaker 1: to have a fair shot at a job, but for audiences,
Speaker 1: no matter what the audiences background, was there a moment
Speaker 1: that just sort of made you almost quit because you
Speaker 1: experienced it in your face, like why didn't you have
Speaker 1: an accent? And one casting director was disappointed that you
Speaker 1: weren't even what do you say? You're not even are
Speaker 1: you even Latin? Are you? And she was disappointed that
Speaker 1: she could that I couldn't put you in that bad
Speaker 1: God damn it, you're not even lack. There were a
Speaker 1: lot of moments where I I kind of thought, maybe
Speaker 1: this isn't the right fit for me. And if I
Speaker 1: can be a little cocky, it's not because I didn't
Speaker 1: think that I had the chops. I just wanted a
Speaker 1: fair shot, right if I wasn't getting an audition because
Speaker 1: I wasn't the best person for the job, so be
Speaker 1: it that happens, right, You go on a hundred auditions,
Speaker 1: you only get one call back. So I get that
Speaker 1: that that I would have been fine with. It was
Speaker 1: the other stuff that I didn't have control over that
Speaker 1: that I thought was um so demoralizing. And then it
Speaker 1: finally dawned on me through these auditions that a lot
Speaker 1: of times you get asked to put on an accent
Speaker 1: to mask bad writing or to mask subpar writing, and
Speaker 1: so the character you're playing automatically gets assigned these racial
Speaker 1: or ethnic signifiers in ways that producers think are helpful
Speaker 1: to advance the comedy, but in reality they don't do
Speaker 1: anything other than connect that character to race, ethnicity, religion,
Speaker 1: which is ultimately like super boring, right, because then you're
Speaker 1: not playing any buddy. Um. I'll give you a quick example,
Speaker 1: and remember the show Sabrina the Teenage which yes, yes,
Speaker 1: with the cat, but the talking cat. So I got
Speaker 1: to audition for this show once and I was super excited.
Speaker 1: It was only three lines, and I needed credits on
Speaker 1: my resume, right, So my agent at the time, who
Speaker 1: was wonderful, she said, here's the info. Here are the
Speaker 1: three lines. I created this whole back story for this
Speaker 1: guy who was supposed to be a kid in Sabrina's
Speaker 1: study group in college. And I was like, all right,
Speaker 1: he's from the Pacific Northwest, and he likes small batch
Speaker 1: organic coffee, and he probably likes Pearl Jam and Nirvana.
Speaker 1: So I wore a flannel to the audition. I thought
Speaker 1: I did well, and I was walking back to my
Speaker 1: car and the casting director ran after me and he goes, hey, man,
Speaker 1: the producers would love for you to do it again,
Speaker 1: this time with an accent. And I was like, okay,
Speaker 1: So again the decision was totally mine, right. I could
Speaker 1: have said no, thank you, but I went back in
Speaker 1: and I thought I needed credit on my resume. The
Speaker 1: job I think paid like five bucks and my rent
Speaker 1: was like five fifty for the month, so that was huge.
Speaker 1: And I said the thing that I usually say when
Speaker 1: people ask for that, where they said we'd love for
Speaker 1: you to do it again with an accent, and I said, sure,
Speaker 1: what kind of accent would you like? I can do
Speaker 1: Brooklyn Scottish, Irish Portuguese. You know, I just like went
Speaker 1: through the list. They were obviously not amused. Uh, And
Speaker 1: so I you know, I made the choice to do it.
Speaker 1: Nobody was forcing me to do that. But you know,
Speaker 1: not to offend anybody that that the racial stuff didn't
Speaker 1: bother me. But the bigger issue as an artist is
Speaker 1: that's a boring choice, man. Like It's just I can
Speaker 1: be funny based on the merits of how I can
Speaker 1: create this character. That's literally what I do. Just let
Speaker 1: me do my thing. I promise you it'll be funny.
Speaker 1: Do you think that there's a space for stereotypes in comedy.
Speaker 1: I definitely think there's a role for stereotypes. Also, the
Speaker 1: you know that old adage of stereotypes come from some
Speaker 1: element of truth, right, and so depending on the comedic bit,
Speaker 1: if you're stripping away context or adding context, or subverting
Speaker 1: something that used to be a stereotype to make it funny.
Speaker 1: For a different reason, I welcome the reality that audiences
Speaker 1: palettes have changed, and so if my job is to
Speaker 1: be funny, I have to evolve with what their pelts
Speaker 1: are and to sort of update my jokes for things
Speaker 1: that people are going to find funny. I don't see
Speaker 1: that as limiting. I actually see that as the opposite,
Speaker 1: where it makes me have to get my chops together.
Speaker 1: You know, well, it's funny because when I when I
Speaker 1: did Suddenly Susan, when I was like, the first time
Speaker 1: I was really well, the first time I was ever
Speaker 1: really really allowed to be funny was and Friends. But
Speaker 1: one of the things that I had to hook into,
Speaker 1: which I didn't resent at all, I loved was the
Speaker 1: physical comedy so that people could laugh at me falling
Speaker 1: on my face or here's the tall girl. Here's the
Speaker 1: big girl. You know, it goes deeper than falling, you know,
Speaker 1: slipping on the banana peel. I mean, it's just always funny.
Speaker 1: You just can't so seeing me get slapped in the
Speaker 1: back with a huge fish and knocked down, or you know,
Speaker 1: or fall off a stool or something, it was sort
Speaker 1: of bizarrely liberating. And I remember thinking, oh my god,
Speaker 1: because they had me falling off something almost every week.
Speaker 1: And I finally said that. I was like, can I
Speaker 1: not all it's just fall off a chair or a
Speaker 1: stool or something. Can you can we make the comedy
Speaker 1: more more funny. But I do think that that's a
Speaker 1: really interesting conversation, and you just make it much more
Speaker 1: sort of intelligent. When you were cast in Van Wilder,
Speaker 1: you said it was a brown catch twenty two. Can
Speaker 1: you explain that? Yeah? Sure, And I'm glad you you
Speaker 1: you asked about Van Wilder when you were talking about
Speaker 1: falling off the stool and getting hit with a fish,
Speaker 1: I'm like, oh, I should. I should talk about Van
Speaker 1: Wilder because it was my first real, big, big movie
Speaker 1: and there was a scene where my character is uh
Speaker 1: the whole movie, he's trying to ask out this woman.
Speaker 1: She agrees to go out with him, and they're they're
Speaker 1: about to try to make love in his room and
Speaker 1: he sets all these scented candles around the room and
Speaker 1: she is putting massage oil on him. He's massaging her.
Speaker 1: By the way, like just keep in mind early two
Speaker 1: thousand's team comedy, so not not particularly high brow. But
Speaker 1: then my character's back catches on fire from one of
Speaker 1: the sentence candles, and the rest of the scene, I'm
Speaker 1: running around the room with my back on fire, which,
Speaker 1: by the way, they that was a practical stunt, so
Speaker 1: I had to wear a prosthetic back. They lit it
Speaker 1: on fire. They're all these guys with essentially hazmat suits
Speaker 1: standing around in case something went wrong. But didn't they
Speaker 1: do it like the first scene was the first day,
Speaker 1: and you're like, why did they do it the first day?
Speaker 1: And they're like, well, because if something happened to you,
Speaker 1: we'd beat We wouldn't have to reshoot all. If you die,
Speaker 1: we can replace you. Really totally, like we'll just replace
Speaker 1: you there. But that's an example of like, yeah, aside
Speaker 1: from the sort of ethnic stereotyping question and all that equation,
Speaker 1: the idea that like I got to light my back
Speaker 1: on fire and run around. You talked to stunt guys
Speaker 1: today and they're like, what producer in the right mind,
Speaker 1: let an actor do that for real? And I was like,
Speaker 1: they said they wanted the wide shot, the special effects
Speaker 1: were too expensive. So we did it and it was
Speaker 1: a blast. But the Brown catch twenty two is something
Speaker 1: that I call it this because it was the thing
Speaker 1: of like, okay, you in order for this is by
Speaker 1: the way, for any actor, right in order to get
Speaker 1: your foot in the door, you have to take small
Speaker 1: parts and that builds up your resume and the credits
Speaker 1: on your resume, and then your agent hopefully can open
Speaker 1: more and more doors for you. The challenge with a
Speaker 1: lot of ethnic performers and a lot of women as well,
Speaker 1: was that the only roles that you're being offered are
Speaker 1: the ones that are sort of reductionists or sort of
Speaker 1: stereotypical and not particularly challenging. And so the Brown Catch
Speaker 1: twenty two was like, do I take those in order
Speaker 1: to get my foot in the door for something bigger,
Speaker 1: because I'm not able to audition for something bigger unless
Speaker 1: I've done those. So it was that sort of thing.
Speaker 1: But but yeah, I mean the the advice that I
Speaker 1: got from the people who I was close to and
Speaker 1: had a lot of mentors who were really good about
Speaker 1: the practicality, which I don't think we talked about nuance
Speaker 1: enough these days, and that you do have to make
Speaker 1: tough choices that are sometimes less than ideal in any
Speaker 1: any job. But then for you, the next sort of
Speaker 1: watershed moment in a way came as You're a Stoner
Speaker 1: when you were in the comedy Harold and Kumart go
Speaker 1: to to White Castle. You know, how did that role
Speaker 1: come about? Really? I think the reason that I got
Speaker 1: that part. And by the way, when I read that script,
Speaker 1: it was the funniest script that I had read. And
Speaker 1: I called John Hurwitz, who I had met at a
Speaker 1: birthday party. He's one of the co creators of the franchise,
Speaker 1: and I called him up and I said, hey, man,
Speaker 1: thank you for sending me the script. You're never gonna
Speaker 1: sell it because studios are never going to green light
Speaker 1: a movie with two Asian American men. So when you
Speaker 1: can't sell it, why don't you call me and like,
Speaker 1: let's find some venture capitalists who can throw together a
Speaker 1: couple of hundred grand and maybe we can make it.
Speaker 1: And he laughed at me and he said, I am
Speaker 1: sorry that that's been your experience, but no, we're selling
Speaker 1: this to a major studio. And I said, no, man,
Speaker 1: I'm telling you the studio is just going to change
Speaker 1: the characters to be black and white. And he interrupted me.
Speaker 1: He's like, well, listen, cal we're making a movie called
Speaker 1: Harold and Kumar Go to Whitecastle, not David and Jason
Speaker 1: go to McDonald's. So we're we are selling this movie
Speaker 1: and they did. They sold it. And one of the
Speaker 1: reasons that I ultimately got the part, you know, there
Speaker 1: was no shortage of actors to play of the roles
Speaker 1: that John cho and I ultimately played, but I was
Speaker 1: one of the few brown actors who had had a
Speaker 1: studio movie under his belt because I had done Van
Speaker 1: Wilder and so let's cast him in this. And of
Speaker 1: course there's there's no stereotyping in Harold and Kumargo to
Speaker 1: White Castle. It's subverting them. And actually, had I not
Speaker 1: gotten Harold and Kumaro to White Castle, which was completely
Speaker 1: career defining for me, and I'm very indebted to the
Speaker 1: fans of that movie. One of my favorite art films
Speaker 1: that I had the chance to work on is called
Speaker 1: The Namesake, based on the novel by Jimpaliery, and I
Speaker 1: would not have gotten the part in The Namesake were
Speaker 1: it not for Harold and Kumar, because Mier and I
Speaker 1: are who directed that film her then fourteen year old
Speaker 1: sons Aren was a huge Harold and Kumar fan, and
Speaker 1: that's basically why I got to audition for the project.
Speaker 1: And you had seen her work and we're so unbelievably
Speaker 1: moved by it. It did mir and I are who
Speaker 1: directed it, had done. One of her first films was
Speaker 1: called Mississippi Massala with Denzel Washington and Street the Choree,
Speaker 1: and I remember seeing that around the same time that
Speaker 1: I was playing the tin man Um. I didn't realize
Speaker 1: fully that I had never really seen people who looked
Speaker 1: like me on screen until I saw this movie, and
Speaker 1: I thought, why am I feeling so seen by a
Speaker 1: film with incredibly flawed, beautifully flawed characters, all of the
Speaker 1: things that make you human. And it kind of dawned
Speaker 1: on me like, Wow, we don't really see ourselves unless
Speaker 1: we're stereotypes or cartoon characters, and so so it really
Speaker 1: it meant a lot, and for for friends I have
Speaker 1: this conversation with friends a lot. If you've always grown
Speaker 1: up with the privilege of seeing characters who look like
Speaker 1: you on screen, you sort of don't feel the thing
Speaker 1: that I couldn't quite put my finger on, which was
Speaker 1: if you don't see yourself, you kind of feel like
Speaker 1: your options in the world might be limited, like maybe
Speaker 1: certain things aren't for you. One of the reasons that
Speaker 1: project was so special was both artistically and in terms
Speaker 1: of who was behind it. A lot of things really
Speaker 1: came full circle for me. The idea that I could
Speaker 1: be this storyteller or this actor was in some way
Speaker 1: because of her early films that that inspired me. Okay,
Speaker 1: first of all, you're you're you're my friend. Now you're
Speaker 1: gonna tell you that now we're friends. But I think
Speaker 1: your life has been so extraordinary. But the pivot to
Speaker 1: politics is seemingly unexpected. How did you get involved? Initially?
Speaker 1: So the I had no desire at all to do
Speaker 1: anything in politics. And for folks who are listening, who
Speaker 1: if the only thing you know about me is that
Speaker 1: I played a stone or three times and then went
Speaker 1: to go work for the president of the United States,
Speaker 1: you are correct to wonder why and how and whether
Speaker 1: I was qualified. So, when I was working on House,
Speaker 1: Olivia Wilde, who you know, fantastic actor and director, She
Speaker 1: was on the show with me, and she had a
Speaker 1: plus one to an Obama campaign event, and I very
Speaker 1: begrudgingly said that I would go with her, even though
Speaker 1: I had no desire to sort of do anything political.
Speaker 1: And I was really inspired by what I saw at
Speaker 1: that event. And so she and I and Tatiana Ali
Speaker 1: and Megalan Chikwauke were the four artists who signed up
Speaker 1: that week. This was back in October of two thousand
Speaker 1: and seven, to go to Iowa, the first state to
Speaker 1: vote in the primary process, to help out the Obama campaign.
Speaker 1: And then I went there and was and fell in
Speaker 1: love with the fact that it was just people who
Speaker 1: were doing something that they believed in and and I
Speaker 1: had the chance to work on that campaign then for
Speaker 1: for the next roughly year or so. And that's that's
Speaker 1: sort of what opened the door. Um. I also think
Speaker 1: what was really eye opening for me was, you know,
Speaker 1: I get why there was a lot of media attention
Speaker 1: when I left the show House to take the sabbatical
Speaker 1: from acting and go go work in the White House
Speaker 1: for a couple of years. Believe they let you out
Speaker 1: of the count community just like that. That's a double
Speaker 1: edged sort. Why you're like thank you, I'm not really
Speaker 1: I mean thank you. The way that that went down,
Speaker 1: I had when I got the offer to work at
Speaker 1: the White House, I had called my agent at the
Speaker 1: time and told her and I said, can you please
Speaker 1: chat with Fox and with House to see if there's
Speaker 1: a way to write me off? And she called back
Speaker 1: almost immediately and said, they said, no, there's no way
Speaker 1: they can do it. So I actually went to David Shore,
Speaker 1: who created House, and I made a point with them,
Speaker 1: sat down with him in his office and I said,
Speaker 1: I know the answer has already been no, and I
Speaker 1: already know that somebody's approached you about this, but I
Speaker 1: got this offer to work for President Obama, and I
Speaker 1: would love for at least you to consider helping me
Speaker 1: do that. And he goes, I had no idea. This
Speaker 1: is the first time hearing of this. You got an
Speaker 1: offer to work at the White House. That's so cool,
Speaker 1: And how did you get the job in the administration
Speaker 1: because you didn't in a sense, you didn't really advocate
Speaker 1: for yourself. No, I didn't. I know this is so silly. Um,
Speaker 1: so I work you would. You had worked for the
Speaker 1: campaign for like a year, and anyone who worked on
Speaker 1: that campaign got a link right around inauguration. I got
Speaker 1: before or after the election that said, if you're interested
Speaker 1: in working for the incoming administration, upload your resume to
Speaker 1: this website at change dot gov. And so I uploaded
Speaker 1: a resume, and I thought, I guess I don't want
Speaker 1: to bother anybody, right, Like, if I'm qualified to work
Speaker 1: at the White House, somebody will call me, But I
Speaker 1: certainly don't want to upload my resume and then make
Speaker 1: a hundred calls like, Hey, just so you guys know,
Speaker 1: I'm super interested, right because A I was already on
Speaker 1: a TV show that was my dream job, and B
Speaker 1: I didn't want it to seem like, oh, cal Penn
Speaker 1: thinks that just because he's on this TV show he
Speaker 1: can ask for a job at the White House. I
Speaker 1: don't know. I didn't know how that worked. So I applied.
Speaker 1: The only person in the world who I told was
Speaker 1: my manager by acting manager. But you had a direct
Speaker 1: line of communication too well by I did, and people
Speaker 1: forget people forget this when you start working for any
Speaker 1: political campaign early enough you get to know the candidate.
Speaker 1: It's usually a very small operation, so you do get
Speaker 1: to know people really well. Part of it is probably
Speaker 1: I felt like there was a bit of imposter syndrome there, like, wow,
Speaker 1: I can't believe that I would actually be considered. And
Speaker 1: then there was another part that was just very self
Speaker 1: conscious and maybe I am really qualified and they'll just
Speaker 1: figure it out. You know. I don't know which it is.
Speaker 1: But at inauguration, Mrs Obama, who I had not met before,
Speaker 1: came over and said something very casual like I hope
Speaker 1: you stay involved. And my manager was standing next to me,
Speaker 1: he was my plus one, and he goes, well, you know,
Speaker 1: Cal applied for a job, right, And she goes, what
Speaker 1: do you mean, and he goes, yeah, he applied for
Speaker 1: a job at the White House and nobody even called
Speaker 1: him back. Sounds like dude, please not now, not now,
Speaker 1: And Mrs Obama says, oh, who did you apply with?
Speaker 1: And I just blurted out, oh, I just put my
Speaker 1: resume on change dot gov, the website that you guys
Speaker 1: sent around, and she looked at me like I was insane,
Speaker 1: and she called the President elect over and made me
Speaker 1: repeat what I had done, and then he basically said, Okay,
Speaker 1: let's if you're serious about this, let's figure out the
Speaker 1: real the reason I even tell the story, Like, hey,
Speaker 1: it's obviously funny and self deprecating and ridiculous. But let's
Speaker 1: say you started at a small startup firm, right, and
Speaker 1: you worked there for a year, and that firm got
Speaker 1: bought out or that firm expanded in a huge way,
Speaker 1: and you were really proud of the work you did
Speaker 1: and you wanted to continue working for the new company.
Speaker 1: Don't just upload your resume. You would call your boss
Speaker 1: and be like, hey, man, I am so proud of
Speaker 1: the work we did together. I would love to be considered.
Speaker 1: And what ways did working because you kind of went
Speaker 1: in with zero experience? I mean that's another Now, what
Speaker 1: moment you all of a sudden you find your moment,
Speaker 1: you find yourself, Oh, I'm in the White House. I'm
Speaker 1: working in the White House, And what ways did that
Speaker 1: change you? I left working in the administration with a
Speaker 1: lot of reverence and inspiration for the process of what's possible.
Speaker 1: And here's why the I have the chance to work
Speaker 1: with thousands and thousands of people who were taking a
Speaker 1: leave of absence from their private sector jobs, just like
Speaker 1: I was. Many of them were teachers or or some doctors,
Speaker 1: some people who were in law school. Um, you know,
Speaker 1: there was no rhyme or reason to people's background necessarily,
Speaker 1: It's just that they wanted to do what they also
Speaker 1: thought was the right thing to do. That's something that
Speaker 1: happens regardless of which administration is in power. Other thing
Speaker 1: was my job was One of my jobs was as
Speaker 1: the President's liaison to young Americans. I worked in the
Speaker 1: Outreach Office. That meant that, because Obama loved hearing ideas
Speaker 1: that he disagreed with, our mandate was to meet with
Speaker 1: people who we agree and disagree with. So that meant
Speaker 1: that in my case, you know, young Republicans were coming
Speaker 1: in to talk about things like healthcare and climate change,
Speaker 1: and we were trying to come up with solutions that
Speaker 1: everybody could sort of compromise on. It didn't mean that
Speaker 1: the President wasn't going to advocate for what he wanted
Speaker 1: and what he thought his base wanted, but it meant
Speaker 1: that that we realized the only way to actually accomplish
Speaker 1: things was to listen to each other and to have
Speaker 1: conversations that are I think, really tough to have today.
Speaker 1: But that was the biggest takeaway from me, was the
Speaker 1: idea that that these things are still possible. I wanted
Speaker 1: to ask you just briefly about your relationship, yeah, because
Speaker 1: it's so beautiful to me. But I'm curious as to
Speaker 1: why or how you were able to keep it private
Speaker 1: for so long. Yeah, of course, it's so funny. When
Speaker 1: I was writing it, there are two chapters in the
Speaker 1: book that have nothing to do with merit. You just
Speaker 1: say it though. It's like in the book I went back.
Speaker 1: I was like, there's a chapter about how my partner
Speaker 1: Josh and I met and fell in love. We've been
Speaker 1: to there eleven years. There's another chapter about going to
Speaker 1: a strip club drunk with friends a couple of years
Speaker 1: after college for a bachelor party. Both of those chapters
Speaker 1: are the only two chapters that I just didn't think
Speaker 1: twice about writing because they had nothing to do with merit.
Speaker 1: They're what editors call a palette cleansing chapter. Because you
Speaker 1: have serious things, you have discovery thing, Okay, here's how
Speaker 1: I achieved this in my line of work. And then
Speaker 1: here's just like a chapter that has nothing to do
Speaker 1: with your success. But then the book came out, and
Speaker 1: I realized my naivete was understandably a lot of journalists,
Speaker 1: especially those who really like profit off of the clicks,
Speaker 1: are like gay Kalpenn writes gay gay only book about
Speaker 1: being gay, very gay book only, And I was like,
Speaker 1: oh no, that's I was like, well, I'm happy to
Speaker 1: share that chapter in the book. That's why I wrote it.
Speaker 1: But I did not think it was gonna distract from
Speaker 1: what the book is actually about. So in retrospect, I
Speaker 1: probably should have like given that chapter to The Atlantic
Speaker 1: or the you know, the New Yorker or something like that,
Speaker 1: with like, hey, do you guys want to run this
Speaker 1: six months before my book comes out. But that said,
Speaker 1: to your point, like there was so much love about
Speaker 1: sharing my story, there was not, I think, a desire
Speaker 1: to sort of hide. I certainly didn't feel like I
Speaker 1: was living a life in the closet. You know. I
Speaker 1: I did come out to myself or figure out my
Speaker 1: own sexuality relatively later in life. You know. I meet
Speaker 1: friends who are like, yeah, I knew when I was eight.
Speaker 1: I was like, man, good for you. I was not
Speaker 1: that kid, you know. It was a little later in
Speaker 1: life for me. But then when my partner Josh and
Speaker 1: I met in d C. He is an incredibly private person,
Speaker 1: sort of like my parents, and so the last thing
Speaker 1: he wants is like we go to movie premieres together.
Speaker 1: He'll come to work events with me, the whole thing.
Speaker 1: But he and my parents when we go to premiers
Speaker 1: that are like cool, we know you have to do
Speaker 1: the photo line and the red carpet because you have
Speaker 1: to sell your movi V. We're going to grab the
Speaker 1: popcorn and go through the side entrance and just see
Speaker 1: you with the seats because it's it's um. You know.
Speaker 1: As someone who has never been able to keep anything private,
Speaker 1: all of my grades from school were published in Life magazine.
Speaker 1: My first period was in People magazine, just because I
Speaker 1: don't know what it was a slow news day, I
Speaker 1: don't know, but yeah, you hit the nail on the head.
Speaker 1: It's not you know. I think people feel that if
Speaker 1: you're choosing not to share a certain aspect of your life,
Speaker 1: that that means that you're either uncomfortable about it or
Speaker 1: you're ashamed about it. And the contrary, I've found for
Speaker 1: many of us who live in the public eye and
Speaker 1: prefer having a certain modicum of privacy is the opposite
Speaker 1: is true. I am so proud and thrilled of who
Speaker 1: I am, of my exactly. It comes from a place
Speaker 1: of respect. Yes, um, do you have a date set
Speaker 1: for the wedding? We were could be a flower girl? Please?
Speaker 1: Oh my gosh, would you when I come? I want
Speaker 1: to drive me. I'm coming all right. I mean this
Speaker 1: is going to know your local to you. I'm really
Speaker 1: good with with family members. Parents will talk your ear off,
Speaker 1: They'll love it. That was the hilarious Cal Pen Keep
Speaker 1: an eye out for pictures of his wedding featuring yours
Speaker 1: truly as a flower girl. I'm just kidding, but Cal,
Speaker 1: if if you want me, I'm I am free. You know.
Speaker 1: If you want to hear more from Cal, pick up
Speaker 1: a copy of his book. You can't be serious. If
Speaker 1: you want to hear more from me, subscribe to this
Speaker 1: podcast Now What with Brookshields on the I Heart Radio app,
Speaker 1: Apple Podcasts or wherever you get your podcasts. Now What
Speaker 1: is produced by the wonderful Julia Weaver with help from
Speaker 1: Darby Masters. Our executive producer is Christina Everett. The show
Speaker 1: is mixed by Bahid Fraser and Christian Bowman. A special
Speaker 1: thanks to Nicky Etre and Will Pearson eight